Winsted, CT Homes

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  $789,000

  • 5 Beds
  • 1.5 Baths
  • 1,258 Sq Ft

  156 Shore Dr, Winsted, CT 06098

  Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor

  Bryan Palladino Showcase Realty, Inc.

  156 Shore Dr, Winsted, CT 06098
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  /20

  $1,150 - $1,550 per month plus fees

  Gilbert Clock Apartments

  Studio - 2 Beds

  13 Wallens St, Winsted, CT 06098

  At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient

  13 Wallens St, Winsted, CT 06098
• 

  $495,000 Sold Jun 09, 2025

  704 W Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 754 Sq Ft
  • Built 1911

  Last Sold Summary

  • 6% Above List Price
  • $656/SF
  • 4 Days On Market

  Current Estimated Value $483,943

  Last Listing Agent KAREN NEWTON William Pitt Sotheby's Int'l

  704 W Wakefield Blvd, Winsted, CT 06098
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  Not Listed For Sale

  174 Wallens St Unit D2, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 2005

  174 Wallens St Unit D2, Winsted, CT 06098

  Last Sold Summary

  • 6% Above List Price
  • $166/SF
  • 39 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Ashley Church Turning Point Realty, LLC
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  /12

  $314,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  230 E Wakefield Blvd, Winsted, CT 06098

  This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.

  Peter D'Addeo Commercial Services Realty

  230 E Wakefield Blvd, Winsted, CT 06098
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  /2

  $1,595 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  50 Benton St, Winsted, CT 06098

  5 room, 1st floor apartment in well established neighborhood. Ranch style. Large eat-in kitchen, 2 bedrooms, den/office. 1 full bath. Ample closets, additional light storage is available in basement. Appliances include, gas range, refrigerator, washer & dryer (in basement). off street parking. Private rear yard.

  JULIE FEDOROVICH Dave Jones Realty, LLC

  50 Benton St, Winsted, CT 06098
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  $800,000 Sold Aug 04, 2025

  266 Perch Rock Trail, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1928

  Last Sold Summary

  • 7% Above List Price
  • $538/SF
  • 0 Days On Market

  Current Estimated Value $834,150

  Last Listing Agent Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
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  Not Listed For Sale

  174 Wallens St Unit D1, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2005

  174 Wallens St Unit D1, Winsted, CT 06098

  Last Sold Summary

  • 17% Above List Price
  • $154/SF
  • 51 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Steve Pener William Pitt
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  /17

  $319,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  25 Center St, Winsted, CT 06098

  Don't miss this unique opportunity to own a multi family residential property and an office space! (Owner currently has permission from the town to create a 2nd residential unit on the first floor) - will have 2.5 baths when completed. Great central location close to all amenities that Winsted has to offer including restaurants, parks, college, public transportation and shopping. First floor

  Tony Goia The Washington Agency

  25 Center St, Winsted, CT 06098
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  /2

  $1,100 per month plus fees

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  12 Beach St Unit 7, Winsted, CT 06098

  Property Id: 1615805Total 8 - 1 BED ROOM UNITS in the building CLOSE to Route 8 & WINSTED Mainstreet, on-site parking, coin operated laundry, REAR BALCONY.

  12 Beach St Unit 7, Winsted, CT 06098
• 

  $269,000 Sold May 05, 2025

  39 Finn St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,175 Sq Ft
  • Built 1880

  Last Sold Summary

  • $229/SF
  • 35 Days On Market

  Current Estimated Value $263,328

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  39 Finn St, Winsted, CT 06098
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  Not Listed For Sale

  174 Wallens St Unit C3, Winsted, CT 06098

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft
  • Built 2005

  174 Wallens St Unit C3, Winsted, CT 06098

  Last Sold Summary

  • 14% Above List Price
  • $128/SF
  • 9 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Amanda Balaski Northwest CT Realty
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  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39 minutes

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
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  /12

  $2,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  188 E Lake St, Winsted, CT 06098

  Welcome to our beautiful lakeside apartment, perfect for professionals seeking a home away from home for long or short term rentals. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity that will make you never want to leave. The modern design and elegant decor create a welcoming and comfortable environment for our

  Annie Simard LPT Realty

  188 E Lake St, Winsted, CT 06098
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  $220,000 Sold Apr 24, 2025

  830 Main St, Winsted, CT 06098

  • 5 Beds
  • 4 Baths
  • 3,115 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Below List Price
  • $71/SF
  • 14 Days On Market

  Current Estimated Value $225,256

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  830 Main St, Winsted, CT 06098
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  Est $276,700 Not Listed For Sale

  17 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft
  • Built 1965

  17 Colony Dr, Winsted, CT 06098

  Last Sold Summary

  • 12% Above List Price
  • $238/SF
  • 72 Days On Market

  Last Sold Price $247,000

  Last Listing Agent David Sartirana Northwest CT Realty
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  $749,900

  • 7 Beds
  • 3 Baths
  • 3,486 Sq Ft

  39 S Main St, Winsted, CT 06098

  THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

  Ryan Horvay Smith & DeGroat Real Estate

  39 S Main St, Winsted, CT 06098
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  /10

  $1,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,199 Sq Ft
  • House for Rent

  22 Upson Ave, Winsted, CT 06098

  Beautiful First-Floor Apartment with Classic Charm and Modern Updates! This spacious first-floor apartment features gleaming hardwood floors, fresh paint, and an updated kitchen. Enjoy the high ceilings and beautiful woodwork that add character and warmth throughout. Conveniently located close to downtown, offering easy access to shopping, dining, and commuting routes.

  Kelly Sullivan Sullivan Real Estate Inc

  22 Upson Ave, Winsted, CT 06098
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  $227,500 Sold Nov 20, 2025

  174 Wallens St Unit H1, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $171/SF
  • 91 Days On Market

  Last Listing Agent Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
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  Est $260,121 Not Listed For Sale

  159 Pratt St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1900

  159 Pratt St, Winsted, CT 06098

  Last Sold Summary

  • 10% Above List Price
  • $201/SF
  • 11 Days On Market

  Last Sold Price $236,500

  Last Listing Agent Cindy Breckheimer Forever Homes Real Estate LLC
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  /31

  $164,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft

  35 Riveredge Dr Unit 35, Winsted, CT 06098

  Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom townhouse set on a slab and overlooking the river. The main level features a living room, dining room, and functional kitchen, perfect for everyday comfort and entertaining. Sliding glass doors lead to a private patio where you can relax and enjoy the peaceful water views. Upstairs offers two comfortable

  Joanne Donne The Washington Agency

  35 Riveredge Dr Unit 35, Winsted, CT 06098
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  /37

  $4,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  880 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this fully renovated, fully furnished 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of

  Matt Crossen Coldwell Banker Realty

  880 W Wakefield Blvd, Winsted, CT 06098
• 

  $190,000 Sold May 15, 2025

  154 Wallens St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • 13% Below List Price
  • $103/SF
  • 20 Days On Market

  Current Estimated Value $195,236

  Last Listing Agent Adam Devine Dorrance Realty

  154 Wallens St, Winsted, CT 06098
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  Est $239,965 Not Listed For Sale

  17 Front St, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1915

  17 Front St, Winsted, CT 06098

  Last Sold Summary

  • 158% Above List Price
  • $58/SF
  • 20 Days On Market

  Last Sold Price $93,000

  Last Listing Agent David Sartirana Northwest CT Realty
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  /38

  $395,000

  • 3 Beds
  • 1.5 Baths
  • 1,909 Sq Ft

  720 Main St, Winsted, CT 06098

  Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,

  Ryan Marconi The Washington Agency

  720 Main St, Winsted, CT 06098
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  $2,450 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  91 Williams Ave, Winsted, CT 06098

  Welcome to this beautifully remodeled and spacious 3-bedroom, 2 full bathroom home in the heart of Winchester. Featuring hardwood floors throughout both the first and second levels, this home offers a warm and inviting layout with an eat-in kitchen that has a center island perfect for everyday living. Enjoy the convenience of a separate laundry room-washer and dryer included, high-efficiency gas

  Suzie Larson Turning Point Realty, LLC

  91 Williams Ave, Winsted, CT 06098
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  $690,000 Sold Feb 06, 2026

  151 Losaw Rd, Winsted, CT 06098

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft
  • Built 2007

  Last Sold Summary

  • 14% Below List Price
  • $234/SF
  • 164 Days On Market

  Current Estimated Value $689,046

  Last Listing Agent Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
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  Not Listed For Sale

  319 Taylor Brook Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft
  • Built 1990

  319 Taylor Brook Rd, Winsted, CT 06098

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 4 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services
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  /13

  $649,900 Pending

  • Land
  • 41.23 Acres
  • $15,763 per Acre

  115 Old Robertsville Rd, Winsted, CT 06098

  Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The home

  Jared Tedesco Litchfield County Real Estate

  115 Old Robertsville Rd, Winsted, CT 06098
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  $277,000 Sold Oct 09, 2025

  12 Cherry St, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,492 Sq Ft
  • Built 1800

  Last Sold Summary

  • 4% Below List Price
  • $186/SF
  • 54 Days On Market

  Current Estimated Value $283,076

  Last Listing Agent Susan MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
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  Est $258,712 Not Listed For Sale

  39 Rockwell St, Winsted, CT 06098

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1900

  39 Rockwell St, Winsted, CT 06098

  Last Sold Summary

  • 20% Above List Price
  • $86/SF
  • 19 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Andrew Vincent Santa Realty
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  /5

  $240,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,874 Sq Ft

  107 Birdsall St, Winsted, CT 06098

  Spacious colonial with 4 bedrooms, 2 full baths, generous size living room, dining room, sitting room, sunroom. Looking for space, this home definitely has it. Harwood floors thorough, granite countertops, marble backsplash, Island in kitchen. Short walk to highland Lake With a little TLC this home will be a GEM! Home being sold AS-IS.

  Jesica Beaulieu Dave Jones Realty, LLC

  107 Birdsall St, Winsted, CT 06098
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  $160,000 Sold Apr 29, 2025

  14 Riveredge Dr Unit 14, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft
  • Built 1986

  Last Sold Summary

  • $161/SF
  • 0 Days On Market

  Current Estimated Value $163,130

  Last Listing Agent Maria Smith KW Legacy Partners

  14 Riveredge Dr Unit 14, Winsted, CT 06098
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  Est $267,558 Not Listed For Sale

  160 Glendale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft
  • Built 1957

  160 Glendale Ave, Winsted, CT 06098

  Last Sold Summary

  • 7% Above List Price
  • $224/SF
  • 85 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Cathy Macias Northwest CT Realty
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  /5

  $295,000 Under Contract

  • Land
  • 51 Acres
  • $5,784 per Acre

  393 Winchester Rd, Winsted, CT 06098

  WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

  Tom McGowan Elyse Harney Real Estate

  393 Winchester Rd, Winsted, CT 06098
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  $230,000 Sold Mar 18, 2026

  106 Rockwell St, Winsted, CT 06098

  • 6 Beds
  • 3 Baths
  • 1,874 Sq Ft
  • Built 1850

  Last Sold Summary

  • 23% Below List Price
  • $123/SF
  • 23 Days On Market

  Current Estimated Value $281,437

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  106 Rockwell St, Winsted, CT 06098
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  Est $309,691 Not Listed For Sale

  153 Mathew Rd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,544 Sq Ft
  • Built 1800

  153 Mathew Rd, Winsted, CT 06098

  Last Sold Summary

  • 7% Above List Price
  • $188/SF
  • 141 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Liz Zakrzewski Coldwell Banker
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  /39

  $920,000

  • 4 Beds
  • 2 Baths
  • 3,088 Sq Ft

  469 Platt Hill Rd, Winsted, CT 06098

  HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

  Marshall Cohen Cohen Agency

  469 Platt Hill Rd, Winsted, CT 06098
• 

  $225,000 Sold Jul 03, 2025

  39 Baker St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1900

  Last Sold Summary

  • $140/SF
  • 166 Days On Market

  Current Estimated Value $230,051

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  39 Baker St, Winsted, CT 06098
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  Est $203,495 Not Listed For Sale

  111 Torringford St Unit 19, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1987

  111 Torringford St Unit 19, Winsted, CT 06098

  Last Sold Summary

  • 3% Above List Price
  • $121/SF
  • 14 Days On Market

  Last Sold Price $197,000

  Last Listing Agent David Sartirana Northwest CT Realty

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